Preparation of alcohol from chlorhydrocarbons.



tageous results.

UNITED STATES PATENT OFFICE.

WALTER E. MASLAND, 0F WILMINGTON, DELAWARE, ASSIGNOR TO E. I. DU PONT DENEMOURS POWDER COMPANY, OF WILMINGTON, DELAWARE, A CORPORA- TION OF NEWJERSEY.

PREPARATION OF ALCOHOL FROM CHLORHYDROCARIBOINS.

No Drawing.

To all whom it may concern Be it known that I, WALTER E. MASLAND, oflVilmington, in the county of Newcastle, and in the State of Delaware,have invented certain new and useful Improvements in Preparation ofAlcohols from Chlorhydrocarbons, and do hereby declare that thefollowing is a full, clear, and exact description thereof.

My invention relates particularly to the production of alcohols, andespecially alcohols of the monohydric parafiin alcohol series. It is,however, applicable to the production of alcohols of many other kinds.

My invention has special reference to the production of alcohols fromchlorhydrocarbons, but itis to be understood that it may be applied tothe production of alcohols from many other halogen derivatives oforganic compounds.

In carrying out my invention, I use as a reagent a compound such, forexample, as one of the oxids or hydroxids of the heavy metals, but Ihave found that Zinc oXid gives much higher yields and that its use ismore advantageous than other compounds. In the case where zinc oxid isused, zinc chlorid is a byproduct, andthis is a. valuable commercialcommodity. I have discovered,

however, that instead of zinc oXid, lead oxidor caustic soda may be usedwith advan- Furthermore, in the place of the oXids and hydroxide, I havediscovered that sodium carbonate may be used.

While my invention is applicable to the treatment of many dilferenthalogen derivatives of organic compounds, I have found it especiallyapplicable to the treatment of amyl and heXyl chlorids. Amyl and heXylchlorids which may be used for this purpose may be obtained byfractionation of a hydrocarbon mixture such as gasolene; thechlorination of the pentanes and hexanes to producemonochlorhydrocarbons; the acetylation of the same with acetic acid andsodium or potassium acetate; the recovery of the olefins thus producedby distillation; and the separation of these olefins by obtaining thechlorolefins which are formed by the action of moderately stronghydrochloric acidat a comparatively low temperature, upon the mixture ofolefins. The chlorhydrocarbons thus obtained may be then mixed withseveral volumes of water and enough zinc Specification of LettersPatent.

Patented Feb. 10, 1914.

Application filed October 11, 1912. Serial No. 725,163.

20 E 01 ZnO m0 2O H OH 21101,

Amyl Zinc Water Amyl Zinc chlorid ox' alcohol ehlorid The reactionhaving been completed, the alcohols are recovered by distillation andthe residual liquid is evaporated to any desired degree foundadvantageous for disposing of the zinc chlorid which it contains.

In carrying out this process it will be found that some olefins areformed as byproducts. These may be used over again to produce alcohols,or in any other desired manner. The alcohols thus obtained are valuablecommercially in many Ways, and it has been found that they areparticularly valuable as a substitute for refined fusel oil. In fact,these alcohols may be used in the various industries in almost everycase Whererefined fusel oil is used. Among other uses that may bementioned, these alcohols have been found to be of considerable valuewhen used with solvents and non-solvents for nitrocellulose.

While I have described my invention above in detail, I wish it to beunderstood that many changes may be made therein without departing fromthe spirit thereof.

I claim:

1. The process which comprises treating a halogen derivative of ahydrocarbon containing an alkyl group, to which latter the halogen isattached, with zinc oxid to transform the same into an alcohol.

2. The process which comprises treating a halogen derivative of analiphatic hydrocarbon with zinc oxid to transform the same into analcohol.

3. The process which comprises treating a halogen derivative of asaturated aliphatic hydrocarbon with zincoxid to transform the same intoan alcohol.

4. The process which comprises treating a halogen derivative of ahydrocarbon of the parafiin series-with zinc oxid to transform same intoan alcohol.

5. The process which comprises treating a mono-halogen derivative of ahydrocarbon of the parafin series with zinc oxid to transform the sameinto an alcohol.

6.The process which com rises treating a chlorin derivative of a hyrocarbon containing an alkyl group, to which latter the chlorin isattached, with zinc oxid to transform the chlorin derivative into analcohol.

7. The process which comprises treating a chlorin derivative of analiphatic hydrocarbon with-.zinc oxid to transform the same into analcohol.

' S. The rocess which comprises treating ;a-chlorin erivative of asaturated aliphatic hydrocarbon with zinc oxid to transform the sameinto an alcohol. A

9. The process which comprises treating a chlorin derivative of ahydrocarbon of the paraflin series with zinc oxid to trans form the sameinto an alcohol.

10. The process which comprises treating a mono-chlorhydrocarbon of theparaffin series with zinc oxid to transform the same into an alcohol.

11. The process which comprises treating from the zinc chlorid solutionand evaporating the latter.

13. The process which comprises treating a saturated chlorhydrocarbonwith zinc oxid to transform the same into an alcohol.

14. The process which comprises treating a saturated chlorhydrocarbonwith zinc oxid to transform the same into analcohol,then separating thealcohol from the zinc chlorid solution and evaporating the latter.

In testimony that I claim the foregoing I have hereunto set my hand. Y

WALTER E. MASLAND.

Witnesses C. R. MUDGE, A. M. GoRMAN.

